Epoxidation of olefins by β-bromoalkoxydimethylsulfonium ylides

Tetrahedron Letters

Volumn 51, Issue 52, 2010, Pages 6830-6834

  Majetich, George ^a   Shimkus, Joel ^a   Li, Yang ^a  

^a UNIVERSITY OF GEORGIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,3,4,6,7,8,9,10 OCTAHYDROPYRIMIDO[ 1,2 A]AZEPINE; ALKENE; ALKENE DERIVATIVE; AZEPINE DERIVATIVE; BETA BROMOALKOXYDIMETHYLSULFONIUM YLIDE; DIMETHYL SULFOXIDE; EPOXIDE; N BROMOSUCCINIMIDE; SULFONIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; DISSOLUTION; ELECTRON; EPOXIDATION; ONE POT SYNTHESIS; OXIDATION;

EID: 78650679658     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.10.068     Document Type: Article

References (39)

1. (a) Dalton, D. R.; Hendrickson, J. R.; Jones, D.J. Chem. Soc., Chem. Commun. 1966, 17, 591-592;
2. (b) Dalton, D. R.; Jones, D. G. Tetrahedron Lett. 1967, 2875-2877;
3. (c) Dalton, D. R.; Dutta, V. P.; Jones, D. G..J. Am. Chem. Soc. 1968, 90, 5498-5501.
4. van Tamelen, E. E.; Sharpless, K. B. Tetrahedron Lett. 1967, 2655-2659.
5. For the participation by other dipolar aprotic solvents, such as acetonitrile, dioxane, or DMF, in comparable reactions, see: (a) Dalton, D. R.; Smith, R. C., Jr.; Jones, D. G. Tetrahedron 1970, 26, 575-581;
6. (b) Boerwinkle, F.; Hassner, A. Tetrahedron Lett. 1968, 3921-3924.
7. Nace, H. R. J. Am. Chem. Soc. 1959, 81, 5428-5430.
8. Eaton, P. J. Am. Chem. Soc. 1962, 84, 2344-2348.
9. (a) Pfitzner, K. E.; Moffat, J. G. J. Am. Chem. Soc. 1963, 85, 3027-3028;
10. (b) Pfitzner, K. E.; Moffat, J. G.J. Am. Chem. Soc. 1965, 87, 5661-5670;
11. (c) Pfitzner, K. E.; Moffat, J. G. J. Am. Chem. Soc. 1965, 87, 5670-5678;
12. (d) Fenselau, A. H.; Moffat, J. G. J. Am. Chem. Soc. 1966, 88, 1762-1765.
13. For more comprehensive reviews of the alkoxysulfonium ion literature, see: (a) Mancuso, A.J.; Swern, D. Synthesis 1981, 165-185;
14. (b) Natus, G.; Goethals, E.J. Bull. Soc. Chim. Belg. 1965, 74, 450-452;
15. (c) Epstein, W. W.; Sweat, F. W. Chem. Rev. 1967, 67, 247-260.
16. For the oxidation of fluoro, chloro, and bromohydrin, see: Fluorine: (a) Thaisrivongs, S.; Pals, D. T.; Kati, W. M.; Turner, S. R.; Thomasco, L. M. J. Med. Chem. 1985, 28, 1555-1558;
17. (b) Myers, A. G.; Barbay, J. K. Org. Lett. 2001, 3, 425-428;
18. (c) Wong, A.; Munos, J. W.; Devasthali, V.; Johnson, K. A.; Liu, H.-W. Org. Lett 2004, 6, 3625-3628;
19. Chlorine: (d) Satoh, T.; Sugimoto, A.; Yamakawa, K. Chem. Pharm. Bull. 1989, 37, 184-186;
20. (e) Satoh, T.; Motohashi, S.; Kimura, S.; Tokutake, N.; Yamakawa, K. Tetrahedron Lett. 1993, 34, 4823-4826;
21. (f) Miura, M.; Toriyama, M.; Motohashi, S. Synth. Commun. 2006, 36, 259-264;
22. Bromine: (g) Noyori, R.; Nishizawa, M.; Shimizu, F.; Hayakawa, Y.; Maruoka, K.; Hashimoto, S.; Yamamoto, H.; Nozaki, H. J. Am. Chem. Soc. 1979, 101, 220-222.
23. (a) Sharma, A. K.; Swern, D. Tetrahedron Lett. 1974, 1503-1506;
24. (b) Omura, K.; Sharma, A. K.; Swern, D. J. Org. Chem. 1976, 41, 957-962;
25. (c) Huang, S. L.; Omura, K.; Swern, D. J. Org. Chem. 1976, 41, 3329-3331;
26. (d) Omura, K.; Swern, D. Tetrahedron 1978, 34, 1651-1660;
27. (e) Mancuso, A. J.; Huang, S.-L.; Swern, D. J. Org. Chem. 1978, 43, 2480-2482;
28. (f) Mancuso, A. J.; Brownfain, D. S.; Swern, D. J. Org. Chem. 1979, 44, 4148-4150.
29. Nakai, H.; Kurono, M. Chem. Lett. 1977, 995-99826.
30. Olah, G. A.; Vankar, Y. D.; Arvanaghi, M. Tetrahedron Lett. 1979, 3653-3656.
31. General epoxidation procedure: To a solution of alkene (200 mg, 1.0 equiv) in 3 mL of anhydrous DMSO at 0 °C was added NBS (1.5 equiv). The reaction was stirred for 20 min. DBU (2.0 equiv) was added to this solution and the reaction was stirred for 30 min. The reaction was quenched at 10 °C with 3 mL of brine, and the precipitated salts were dissolved by the addition of 1.5 mL distilled water. The solution was extracted three times with ether, and the organic portions were combined, washed with brine, and dried over anhydrous MgSO4. Filtration, followed by concentration at reduced pressure on a rotary evaporator, afforded a crude residue that was purified on silica gel 60 (230-400 mesh ASTM) using appropriate mixtures of distilled, reagent-grade pentane and ether.
32. Choubal, M. D.; Basset, J. Y. Org. Prep. Proceed. Int. 1991, 23, 667-670.
33. (a) Albright, J. D.; Goldman, L. J. Am. Chem. Soc 1965, 87, 4214-4216;
34. (b) Albright, J. D.; Goldman, L. J. Am. Chem. Soc. 1967, 89, 2416-2423;
35. (c) Albright, J. D. J. Org Chem. 1974, 39, 1977-1979.
36. (a) Corey, E. J.; Kim, C. U. J. Am. Chem. Soc. 1972, 94, 7586-7587;
37. See also: (b) Meerwein, H.; Zenner, K.-F.; Gipp, R. Liebigs Ann. Chem. 1965, 688, 67-77.
38. Taber, D. F.; Liang, J.-L. J. Org. Chem. 2007, 72, 431-434.
39. Ahmad, S. M.; Braddock, D. C.; Cansell, G.; Hermitage, S. A.; Redmond, J. M.; White, A. J. P. Tetrahedron Lett. 2007, 48, 5948-5952.